3-Chloro-4-methylphenyl isocyanate → 4-Bromomethyl-3-chlorophenylisocyanate

Participants

Reaction Steps

To a stirred solution of 100.0 grams (0.597 mole) of 3-chloro-4-methylphenylisocyanate in 1000 ml of carbon tetrachloride, under an argon atmosphere were added 116.8 grams (0.656 mole) of N-bromosuccinimide and 5.0 grams (0.021 mole) of benzoyl peroxide. The reaction mixture was warmed to reflux where it stirred for 4 hours; then it was allowed to cool to ambient temperature as it stood for 16 hours. The mixture was filtered and the filtrate concentrated under reduced pressure to give 147.1 grams of 4-bromomethyl-3-chlorophenylisocyanate as a residual oil. The oil was used without further purification.

Provenance & Evidence